Greenbrier Mall was the second closest major shopping center to our location in the Princess Anne area of Virginia Beach, but we rarely ever went there. It was a mystery to me; one I wanted to research and get to the bottom of. I remember as we would approach the Greenbrier Parkway exit on Interstate 264, I'd struggle to see the slightest segment of the mall as we drove past. Alas, even though the super-regional was located right next to the freeway, I don't remember ever getting more than a quick peek of Sears’ white washed walls from my back seat vantage point. It seemed like it was trying to obscure itself from me.
The first time that I did get a good look at what the interior of Greenbrier had to offer, it was actually on television. WAVY TV10 News was doing an entire broadcast from a location in five of the major cities of Hampton Roads. Their Chesapeake location was to be Greenbrier Mall. Even though, at that age, I thought that the news was the most monotonous and mind-numbing experience outside of long division, I couldn't wait for six p.m. to arrive that evening. I remember focusing on the corridors and mallways located just behind Terry Zahn as he reported on another savings and loan scandal or the cold war, whatever was big news back then. From our 27 inch wood console tv, Greenbrier looked immense. The skylight feature over center court seemed to go on forever and the place looked to me like it was three levels. Three whole stories! I had to see it for myself.
I have to admit that when I finally did visit Greenbrier Mall I was a bit disappointed. My expectations were set rather high, and I was hoping to experience a monstrous monument to capitalism. But what I found was a simple two level facility (albeit the only fully double-tiered enclosed concourse in South Hampton Roads at that time) with only two anchors and not a whole lot more. What I did like was that the mall was on a graded piece of real estate; entrances were accessible on both the first and second levels while some portions of the building were "buried." In addition to that unique element for the region, Greenbrier Mall was rather bright for a mall designed during the late seventies. There were the standard wooden floors beneath wide ceilings with wooden accents, but that abundance of timber was in the burnished and lighter shades of the pine variety. I also remember the food court was kind of hidden in a small cubby hole on the second level outside of the massive center court. But I'm not completely sure if I'm remembering this correctly as, on my next visit, it was actually located closer to Sears.
Greenbrier Mall Mallmanac ca. 1999. View the full PDF version here.
Greenbrier Mall opened in 1981 as the growing bedroom community of Chesapeake's first enclosed shopping center. At that time, it had only two anchors, Sears and Miller & Rhoads. There was clearly room for two other majors to be added later, and it wasn't long before they were. First, around 1987, a Hess's was erected at the building's southeastern end. I remember the Virginia Pilot's printing a big write-up on the new outlet, one that was much larger than the average Hess's venue. I rode my bike all the way out to the still mysterious mall one summer day just to finally see the neoteric novelty with its new-store smell and my favorite nameplate. I'll never forget how the escalators were encased in glass while multi-colored lights enhanced the experience. It was the closest my underage mind had ever come to trippin'. Just a year or two later, Leggett built one of their trademark diamond-shaped emporiums on the northeastern pad, giving the mall the footprint it has to this day.
Greenbrier Mall Mallmanac ca. 2000. View the full PDF version here.
There was a little anchor shuffling as the years passed. Miller & Rhoads first became Hecht's before being taken over by Macy's. Hess's was eventually lost to Dillard's while Leggett's tenure at Greenbrier was short lived. Dillard's took over their space as well, using it as a second location while they expanded their original pad. When they consolidated into one location, JCPenney used that opportunity to join the tenant list. Sears, in what seems to be the norm for them, remains the oldest extant anchor.
-UPDATE- 1- The massive former Sears store (Source) 2- Greenbrier mall from the south. (Source)
Greenbrier continues to serve its market well, although still not with an identity that its area retail peers seem to enjoy. But even as Tower Mall has faded away and Military Circle as well as the younger
Chesapeake Square struggle to remain relevant, Greenbrier continues to hold its own in a crowded market.
-UPDATE- Greenbrier Mall Mallmanac ca. 2015. View the full PDF version here.
In news that was a surprise to absolutely no one, the oldest extant anchor at Greenbrier Mall, Sears, exited their final remaining full size location in the southside in 2018. The other three anchors still remain and seem to do pretty well, while the mall itself still boasts a rather robust list of tenants. Its only competition in the municipality, Chesapeake Square, while still open, has seemingly thrown in the towel and seems to be headed for a full redevelopment, so it’s good to see that the older Greenbrier still draws in the crowds.
Greenbrier Mall lease plan ca. 2021. View the full PDF version here.
An entertainment complex which was to include a hotel, several bars, restaurants and a gambling parlor known as Rosie’s Gaming Emporium was proposed for the former Sears space but traffic concerns scuttled the idea. Today the nearly 200,000 square foot building hosts a temporary location for Dick’s Sporting Goods while the bottom tier remains unoccupied.
-UPDATE- 1 & 2- Sears. 3 & 4- Miller & Rhoads/ Hecht’s/ Macy’s. 5 & 6- Hess’s/ Proffit’s/ Dillard’s. 7 & 8- Leggett/ Dillard’s/ JCPenney.
At this point, as
MacArthur Center and Chesapeake Square circle their respective drains ready to join Pembroke, Military Circle and Tower Mall in the great parking lot in the sky, most predict that South Hampton Roads can support only one major enclosed shopping center by the time the dust settles. By most accounts, the lone victor will be Lynnhaven. This doesn’t bode well for Greenbrier, the forgotten, anonymous white walled monolith of Chesapeake.
-UPDATE- Greenbrier Mall pamphlet ca. 2022. View the full PDF version here.
-15 March 2026
Not more than a few minutes after dropping off my luggage at my hotel room in downtown Norfolk, I was off to explore the initial mall on my list. On the short drive I had been taking in all of the sites of south Norfolk and its massive amount of Naval industry when I arrived at the double tiered and largest shopping center in Chesapeake, Greenbrier Mall.
1 to 3- Greenbrier Mall’s front entrance located between the former Sears and Miller & Rhoads. 4 to 8- The now vacant Sears store.
With its mid-eighties jingle “Simply terrific... Greenbrier Mall” playing repeatedly in my head, I entered at the front facing, upper level entrance closest to the former Sears. The restaurant located next to the doorway, Twisted Crab, was still open for business so I maintained hope that the shopping center had sustained its momentum through these unforgiving times. Then I stepped inside.
Greenbrier Mall Mallmanac ca. 2024. View the full PDF version here.
I was greeted by the same architectural framework that I was familiar with after all of these years, though the wooden floor was now covered in carpet and the pine slats on the ceiling had been painted an unappealing shade of beige. But, unlike the layers of overdone cosmetic work Lynnhaven has had, the Greenbrier I grew up with was still very much right there, wrinkles and all.
1 to 6- Outside the food court and the lower level mall entrance next to JCPenney. 7 to 10- The JCPenney store, still sporting the same façade as its predecessor, Leggett.
Unfortunately, the merchants selling their wares simply weren’t. The main concourse between the darkened Sears and center court was lined with gates in the down position and few shoppers to peruse them if they were occupied. And, upon closer inspection, I noticed that the small, half tube skylights over the main concourse were dingy and covered in dirt.
1 & 2- Greenbrier Mall’s common area exterior between Dillard’s and JCPenney. 3 to 5- Dillard’s in the spot once occupied by Hess’s and Proffitt’s. 6 & 7- The original and expansion portions of the former Miller & Rhoads and Hecht’s store is easily defined. 8- Macy’s entrance on the expansion.
Fortunately, as I neared center court, both open stores and patrons to give them their money became more numerous. Then I arrived at what has to be one of my favorite mall center courts of all time. With its soaring, nearly wedding cake like tiers of glass and metal, I could see why younger me erroneously though that Greenbrier Mall was three levels.
With the double tiered interior entrances to Macy’s behind me, Dillard’s to my right and JCPenney in front, I stood beneath the highest point of Greenbrier Mall, admiring how through its single renovation it managed to keep so much of its original personality. I’m pleased to have taken this moment, as subsequent visits to the region’s other malls would leave me, for the most part, disappointed in their changes.
1 to 6- The northernmost part of the main concourse where it meets the now darkened Sears. 7 to 10- Greenbrier Mall’s upper level food court.
Besides Dillard’s exterior, which completely conformed to their bland template, the façade was nearly completely untouched. One of my favorite parts will always be the expansion of what was originally Miller & Rhoads, where Hecht’s made little effort to blend the newer building with the old. Even the seams are still very apparent, as well as the former occupant’s diminutive and nearly unnoticeable entrances complete with their black glass overhangs.
From the outside the best views of Greenbrier Mall were from a distance, where the skylight over center court could be seen rising like a mountain over an otherwise unremarkably planar roofline. JCPenney’s façade remained unchanged from what once housed Leggett while Sears, with its fading label scars, looked much the same, though years of vacancy and neglect were taking their toll.
The main concourse between the food and center courts still reflects much of the original design of Greenbrier Mall.
I ended my exploration on the bottom level mall entrance abutting the food court. It was a great start to this trip down into the recesses of my teenage mind. And, although Greenbrier wasn’t as successful as I would have liked, its more than eighty percent occupancy rate is admirable considering today’s retail environment as well as its recent history.
1 & 2- The main concourse abutting center court. 3 to 8- Greenbrier Mall’s impressive and expansive center court, definitely a top five for me.
Chattanooga based CBL Properties, the former owners, defaulted on a 62 million dollar loan payment in 2022 and the building, minus Dillard’s, was put up for auction early in 2025. The winning bidder was a local developer, Sifen Inc, which paid 22.5 million dollars for the property. What’s done from this point remains to be seen.
Greenbrier Mall Mallmanac ca. 2025. View the full PDF version here.
It seems to me that Greenbrier Mall’s best bet may be to downsize. The three occupied anchors and most of the leased square footage is huddled around center court, so I can envision a redevelopment involving eliminating the former Sears store and most of its adjoining concourse. The food court, nearly empty as of this writing, could be moved back to its former cubby hole between JCPenney and Dillard’s.
1 to 3- The mall opening to Macy’s. 4 & 5- The 1987 built corridor that leads to Hess’s. 6 to 8- Where Dillard’s meets Greenbrier Mall. 9- Looking toward center court from the bottom level of the former Proffit’s concourse. 10- JCPenney’s entrance at the end of their truncated wing.
My main hope is that a gem like Greenbrier Mall never shares the same fate as so many other of its peers. That would be that what was once a meeting place for an entire generation is completely erased for another fulfillment center like
Mall of Memphis or
East Towne Mall.
